Acetic Acid → (1-{N'-(4-Bromobenzyl)-N'-[3-(2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-3-hydroxy-4-phenyl-butyl]-hydrazinocarbonyl}2,2-dimethylpropyl)carbamic acid methyl ester

HRID 1158535Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1158535
[CH2:1]([C@:8]([OH:24])([CH2:21][CH2:22]O)[C:9]([NH:11][C@H:12]([C:17](=[O:20])[NH:18][CH3:19])[C:13]([CH3:16])([CH3:15])[CH3:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:25][O:26][C:27](=[O:46])[NH:28][C@H:29]([C:34]([NH:36][NH:37][CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=1)=[O:35])[C:30]([CH3:33])([CH3:32])[CH3:31].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[CH3:25][O:26][C:27](=[O:46])[NH:28][CH:29]([C:34]([NH:36][N:37]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([Br:45])=[CH:41][CH:40]=1)[CH2:22][CH2:21][C:8]([C:9](=[O:10])[NH:11][CH:12]([C:17](=[O:20])[NH:18][CH3:19])[C:13]([CH3:16])([CH3:14])[CH3:15])([OH:24])[CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:35])[C:30]([CH3:33])([CH3:32])[CH3:31]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 11710481{(1S)-1-[N'-(4-Bromo-benzyl)-hydrazinocarbonyl]-2,2-dimethyl-propyl}-carbamic acid methyl esterHCID 44818994(2S)-2-Benzyl-N-((1S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-2,4-dihydroxy-butyramide

Produkt 1

HCID 68677269(1-{N'-(4-Bromobenzyl)-N'-[3-(2,2-dimethyl-1-methylcarbamoyl-propylcarbamoyl)-3-hydroxy-4-phenyl-butyl]-hydrazinocarbonyl}2,2-dimethylpropyl)carbamic acid methyl esterAusbeute 28 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 111,2-DichloroethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of (2S)-2-Benzyl-N-((1S)-2,2-dimethyl-1-methylcarbamoyl-propyl)-2,4-dihydroxy-butyramide (52S) (0.337 g, 1.00 mmol), IBX (0.560 g, 2.0 mmol) and 10 mL 1,2-dichloroethane in a reaction vial sealed with a screw cap was heated at 80° C. for 2 h. The resulting suspension was transferred to a 20 mL syringe and filtered through a syringe filter into a solution of hydrazide (9) (0.372 g, 1.00 mmol) in 15 mL DCE in a flame dried 50 mL round-bottom flask equipped with a septum. To this was added acetic acid (0.12 mL 2.0 mmol), mixture was stirred for 10 min and then sodium triacetoxyborohydride (0.636 g, 3.0 mmol) was added. The septum-sealed flask was flushed with nitrogen and the reaction was stirred at room temperature for 24 h. The reaction was quenched by addition of water and volatiles were evaporated. The residue was dissolved in 50% MeCN/water and purified by preparative RP-LC-MS (repeated 1 mL injections) to give 0.191 g of the title compound (28% yield).

Aufarbeitung

  1. customin a reaction
  2. customvial sealed with a screw
  3. customcap
  4. customThe resulting suspension was transferred to a 20 mL syringe
  5. filtrationfiltered through a syringe
  6. customdried 50 mL round-bottom flask
  7. customequipped with a septum
  8. customThe septum-sealed flask was flushed with nitrogen
  9. stirringthe reaction was stirred at room temperature for 24 h
  10. customThe reaction was quenched by addition of water and volatiles
  11. customwere evaporated
  12. dissolutionThe residue was dissolved in 50% MeCN/water
  13. custompurified by preparative RP-LC-MS (repeated 1 mL injections)

Quellen und Nachweise

ORD-Eintrag
ord-18c2a826641a4aa18a74b4a12d953432
Quelldatensatz
uspto-grants-2010_10
Patentnummer
US07807677B2

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